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Friends With Benefits Lineart

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GIRL: "Hey, Lupe! Missed you! *hugs* Who's the cute arm candy?"
LUPE: "This is my friend, Jessie."
JESSIE: "Friend?"
LUPE: "Yeah. Friend...we're just friends..."
JESSIE: "...Good friends..."
LUPE: "...Right...good friends..."
JESSIE "...VERY good friends..."
LUPE: "......very...good friends..."
JESSIE: "..........I'm his bitch."
LUPE: "Jessie!"
JESSIE: "What?"

Jessie and Lupe...for lack of a better word...it's complicated.

Ever since they first met, Jessie and Lupe have been this weird flux of on again-off again relationships, middle of the night kidnappings and a cat and mouse game that may never come to an end. But no matter how many lovers Jessie has had in his life his heart will always beat a little bit faster for the hunky gray wolf. And no matter how many lovers Lupe has, he always finds himself going back to Jessie. One would think that they're meant to be, but it's a little difficult to have a serious relationship when there's only one thing that seems to keep it going: bondage.

Jessie and Lupe first met at a fetish party at Aria's friend's place. That night, Aria was planning to get Jessie tied up in front of everyone to embarrass him and give him a fun and kinky night. Aria was double-crossed by her friend and the siblings both ended up bound and gagged. They were ogled and played with, but at some point when no one was looking, Jessie was whisked away into a bedroom and was thoroughly taken advantage of. At first he was scared that he was going to be raped, but the stranger didn't simply have sex with Jessie, he actually made love to Jessie. It was warm, passionate and sensual. As soon as it was over, the stranger disappeared, leaving Jessie a little heart broken.

Weeks later, Aria took Jessie to a normal house party. Aria went on her own within minutes of arriving. Leaving Jessie to fend for himself. He tried to mingle and make friends. He started mostly attracting guys, but once word got out about him being a crossdresser, it spread quickly and Jessie was suddenly isolated. But then he was approached by a handsome and hunky gray wolf named Lupe. They danced a little, drank a little and talked about interests, current events and things were clicking between them. Then they were interrupted by a group of couples asking about Jessie being a crossdresser and making fun of him about it. Jessie was so embarrassed he left the party crying. Lupe found him sitting next to Aria's car sobbing and sat down next to him. He confessed that he knew Jessie was a crossdresser the whole time. This not only surprised Jessie, but compelled to ask if Lupe was gay. Lupe admitted to being bi-sexual, but only because he had thing for crossdressing girl bois. It seemed to good to be true to Jessie, but he couldn't sense any deceit. Lupe then offered to take Jessie home. Jessie happily accepted, but not before telling Aria. Lupe escorted Jessie in like a gentleman which convinced Jessie to ask invite him in for coffee. Lupe couldn't resist. They talked for another hour and then Lupe talked Jessie into showing him his room. Lupe was surprised at how nerdy Jessie was, but it didn't bother him that much. When Jessie had to use the restroom, it gave Lupe the opportunity search through Jessie's stuff. He knew what he was looking for though and found it just in time for Jessie to finish. When Jessie exited the restroom Lupe surprised him by dangling some rope and a ballgag in front of him. Jessie was shocked and a bit upset that Lupe snooped through his room, but the sight of the bondage toys aroused him and Lupe talked Jessie into letting him tie Jessie up. Once Jessie was all tied up and helpless the two had a few passionate kisses and then Lupe shoved the ballgag in Jessie's mouth and positioned him against the wall where Lupe wasted no time dropping his pants and Jessie's panties. After a little lube Lupe made love to Jessie. In the middle of the sex Jessie was reminded of the night a total stranger made love to him at a party. The experience felt exactly the same. Jessie couldn't believe that this great guy he just met was the same pervert who more or less raped him. Jessie never really saw it that way though. He was even more into Lupe now, knowing that he was capable of making love to him like this consistently and that Lupe was totally into Jessie. When he finished, Lupe laid Jessie onto the bed and climbed in next to him. Jessie fell asleep still bound and gagged and in Lupe's arms. Lupe gave Jessie a kiss on the forehead and the relationship was born.

At first they dated for about a month, sharing in each other's interests and sleeping together every other night on average sometimes everyday for a week for one week each month. Jessie even talked Lupe into moving in together. That's when things started going south. The found a little time apart was good for them as being together all the time was getting on each other's nerves. Jessie learned that Lupe had a dozen or more friends who were ex-girlfriends and would try to see one of them every other day and sometimes everyday. Jessie's immaturity and bubbliness sometimes got on Lupe's nerves.
In short, things weren't working out and Lupe's suspicion of cheating upset Jessie. They ended up breaking up and didn't talk for months. Then Lupe came a calling, wanting to get back with Jessie, who was reluctant after being hurt the way he was. A hot night of bondage and sex changed his mind and they were dating again. They tried to get serious again, but they had difficulty getting past each other's quirks adn it seemed that Lupe hadn't given up on all his ex's and was still seeing one or two of them. Arguments ensued, tears were shed, objects were thrown and they finally had enough and just split with not a word to each other. A few more months passed and Jessie was getting depressed, wanting to get over Lupe, but the lack of lovers who were matching up to his sexual prowess and warmth and love (when he wasn't being a womanizer) kept him from moving on. He actually sot out Lupe and found him at one of the bars he frequented. He was alone and depressed after having attempted to get with another woman, but was stopped by thoughts of Jessie running through his head. The two talked over a few beers and they both came to the realization that they're love for each other was more physical than emotional. Lupe loved tying Jessie up and having sex with him and Jessie loved being tied up by Lupe and having sex with him. Bondage seemed to be the only thing that linked them together and it was a link so strong that it seemed nothing could break it. With a kiss and a hug they agreed to be friends and from time to time when their urges drove them to, they'd be lovers.

Today they are, if nothing else, good friends. They care for each other and respect each other and go out of their ways to help each other when needed. The have become best of friends and get along well. Of course, their sexual urges always get the better of them as often as once a week they meet up and engage in hot in-bondage sex. Whenever they need a date or a close friend to confide in they're there for each other. At times when people watch them from afar, the two seem to resemble a married couple. They'll usually deny being in love with each other, but sometimes certain situations and moments will compel each other to show signs that they really do love each other. Until they can sort this whole mess out between them, they will always be a complicated pair.

The conversation above was spurned on by an ex-girlfriend of Lupe's greating him in a friendly manner. Jessie was already feeling close and loving towards Lupe having been invited to a party by him and hit with a slew of compliments by the wolf. Jealousy was coming over Jessie and he felt compelled to establish the he and Lupe were more than friends: that they were lovers.

Lupe can't bring himself to admit that he really loves Jessie that he would be the only Lupe would ever consider settling down with. As much as he loves Jessie though, he can't help but only think about how good the fox looks in a miniskirt and high heels, all tied up and gagged.
Jessie can't admit to himself that getting tied up and fucked and treated like a possession wouldn't be such a bad way to live. After all the thought of how Lupe ties his knots and works Jessie up before sex is always enough melt. But Jessie doesn't want to just be a piece of meat ALL the time. Maybe half the time.

In the end it's up to each of them to make some kind of a compromise if they want to have a future together that involves more than just ropes, ballgags, nipple clamps and anal sex. Then again sex is important to a lasting relationship. Even if that's all the relationship is based on. :P

This piece was drawn for me by the wonderful Da_Fluffeh over at FA, but it's not done yet. Still needs to be colored. ^_^



Jessie and Lupe © Me ^_^

Art by Da_Fluffeh [link]
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